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Calley Pittman has extensive work experience, starting with their role in the United States Air Force as an Enlisted member from 1988 to 1990. After that, they worked at PITTMAN, initially as Vice President/ CEO from July 1993 to June 2018, and then as President/ CEO from June 2018 onwards.

Calley Pittman attended the University of Maryland - Robert H. Smith School of Business from 1991 to 1993, where they obtained a Bachelor's degree in Accounting and Business/Management. Calley also attended the University of Maryland from 1990 to 1993, earning another Bachelor's degree in the same field of study. Before attending the University of Maryland, Pittman had studied Electrical, Electronic, and Communications Engineering Technology/Technician at the Community College of the Air Force from 1988 to 1989.